NP-MRD: Showing NP-Card for Stephavanine (NP0067385)

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Record Information

Version

2.0

Created at

2022-04-28 12:14:44 UTC

Updated at

2022-04-28 12:14:45 UTC

NP-MRD ID

NP0067385

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Stephavanine

Description

STEPHAVANINE belongs to the class of organic compounds known as hasubanan alkaloids. These are alkaloids with a structure based on the hasubanan skeleton, a tetracyclic propellane. Stephavanine is found in Stephania abyssinica and Stephania abyssinica Walp. . Based on a literature review very few articles have been published on STEPHAVANINE.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282214142D          

 36 42  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282214142D          

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M  END
> <DATABASE_ID>
NP0067385

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C(=O)O[C@H]1C[C@]23CCN[C@@]22C[C@H](O[C@@]2(OC)[C@H]1O)C1=CC2=C(OCO2)C=C31

> <INCHI_IDENTIFIER>
InChI=1S/C26H27NO9/c1-31-17-7-13(3-4-16(17)28)23(30)35-21-10-24-5-6-27-25(24)11-20(36-26(25,32-2)22(21)29)14-8-18-19(9-15(14)24)34-12-33-18/h3-4,7-9,20-22,27-29H,5-6,10-12H2,1-2H3/t20-,21-,22-,24-,25-,26-/m0/s1

> <INCHI_KEY>
BTDVYOKUHWMJJD-UWBSNJKQSA-N

> <FORMULA>
C26H27NO9

> <MOLECULAR_WEIGHT>
497.5

> <EXACT_MASS>
497.168581453

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
49.17369039813322

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,11S,13S,14R,15S,16S)-15-hydroxy-14-methoxy-5,7,21-trioxa-20-azahexacyclo[11.4.3.1^{11,14}.0^{1,13}.0^{2,10}.0^{4,8}]henicosa-2,4(8),9-trien-16-yl 4-hydroxy-3-methoxybenzoate

> <ALOGPS_LOGP>
1.30

> <JCHEM_LOGP>
1.5540662605321227

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.239059046461529

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.73637275503349

> <JCHEM_PKA_STRONGEST_BASIC>
9.344372268034965

> <JCHEM_POLAR_SURFACE_AREA>
124.94000000000001

> <JCHEM_REFRACTIVITY>
123.0387

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.55e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,11S,13S,14R,15S,16S)-15-hydroxy-14-methoxy-5,7,21-trioxa-20-azahexacyclo[11.4.3.1^{11,14}.0^{1,13}.0^{2,10}.0^{4,8}]henicosa-2,4(8),9-trien-16-yl 4-hydroxy-3-methoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       7.309   1.458   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.988  -0.048   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.523  -0.523   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.379   0.508   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.701   2.015   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.166   2.489   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.249   3.497   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.149   3.667   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.499   2.042   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.825   1.720   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.819   0.466   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.091   1.360   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.122   2.905   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.639   2.712   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       2.056  -0.928   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.509  -0.915   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.219   0.515   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.759   0.491   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.301  -2.225   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.840  -2.178   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.569  -0.822   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.651  -3.488   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.921  -4.844   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.732  -6.154   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.271  -6.107   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.000  -4.751   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.190  -3.441   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -6.539  -4.704   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -7.349  -6.014   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -5.081  -7.417   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.133   3.584   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.913   2.656   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.151   1.740   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.321  -0.820   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.466   0.210   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.841   1.617   0.000  0.00  0.00           O+0
CONECT    1    2    6   36                                                  
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   31                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   17   32                                             
CONECT   10    9   11   14   31                                             
CONECT   11   10    4   12   15                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16    9   18                                                  
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   22                                                       
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   25                                                            
CONECT   31   10    7                                                       
CONECT   32    9   33                                                       
CONECT   33   32                                                            
CONECT   34    2   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35    1                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₇NO₉

Average Mass

497.5000 Da

Monoisotopic Mass

497.16858 Da

IUPAC Name

(1S,11S,13S,14R,15S,16S)-15-hydroxy-14-methoxy-5,7,21-trioxa-20-azahexacyclo[11.4.3.1^{11,14}.0^{1,13}.0^{2,10}.0^{4,8}]henicosa-2,4(8),9-trien-16-yl 4-hydroxy-3-methoxybenzoate

Traditional Name

(1S,11S,13S,14R,15S,16S)-15-hydroxy-14-methoxy-5,7,21-trioxa-20-azahexacyclo[11.4.3.1^{11,14}.0^{1,13}.0^{2,10}.0^{4,8}]henicosa-2,4(8),9-trien-16-yl 4-hydroxy-3-methoxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C(=O)O[C@H]1C[C@]23CCN[C@@]22C[C@H](O[C@@]2(OC)[C@H]1O)C1=CC2=C(OCO2)C=C31

InChI Identifier

InChI=1S/C26H27NO9/c1-31-17-7-13(3-4-16(17)28)23(30)35-21-10-24-5-6-27-25(24)11-20(36-26(25,32-2)22(21)29)14-8-18-19(9-15(14)24)34-12-33-18/h3-4,7-9,20-22,27-29H,5-6,10-12H2,1-2H3/t20-,21-,22-,24-,25-,26-/m0/s1

InChI Key

BTDVYOKUHWMJJD-UWBSNJKQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Stephania abyssinica	LOTUS Database	35616633
Stephania abyssinica Walp.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hasubanan alkaloids. These are alkaloids with a structure based on the hasubanan skeleton, a tetracyclic propellane.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Hasubanan alkaloids

Sub Class

Not Available

Direct Parent

Hasubanan alkaloids

Alternative Parents

Substituents

Hasubanan skeleton
Phenanthrene
M-methoxybenzoic acid or derivatives
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
Methoxyphenol
Tetralin
Benzoate ester
Dihydroindole
Indole or derivatives
Benzodioxole
Benzoic acid or derivatives
Phenoxy compound
Anisole
Phenol ether
Benzoyl
Methoxybenzene
Phenol
1-hydroxy-2-unsubstituted benzenoid
Ketal
Aralkylamine
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Tetrahydrofuran
Pyrrolidine
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Amino acid or derivatives
Acetal
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Secondary amine
Secondary aliphatic amine
Ether
Monocarboxylic acid or derivatives
Alcohol
Organic nitrogen compound
Amine
Organic oxygen compound
Organopnictogen compound
Organooxygen compound
Organic oxide
Organonitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.3	ALOGPS
logP	1.55	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	8.74	ChemAxon
pKa (Strongest Basic)	9.34	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	124.94 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	123.04 m³·mol⁻¹	ChemAxon
Polarizability	49.17 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00025130

Chemspider ID

28425442

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92043404

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Stephavanine (NP0067385)

MOL for NP0067385 (Stephavanine)

3D MOL for NP0067385 (Stephavanine)

3D SDF for NP0067385 (Stephavanine)

3D-SDF for NP0067385 (Stephavanine)

PDB for NP0067385 (Stephavanine)

3D PDB for NP0067385 (Stephavanine)

SMILES for NP0067385 (Stephavanine)

INCHI for NP0067385 (Stephavanine)

Structure for NP0067385 (Stephavanine)

3D Structure for NP0067385 (Stephavanine)